US5182315AExpiredUtility

Photocurable silicone gel composition, and method of making the same

53
Assignee: LOCTITE CORPPriority: Nov 19, 1990Filed: Nov 19, 1990Granted: Jan 26, 1993
Est. expiryNov 19, 2010(expired)· nominal 20-yr term from priority
Inventors:Hsien-Kun ChuRobert P. CrossDavid I. Crossan
C08G 77/50C08L 83/14C09D 183/14C09K 3/1018C09K 2003/1062C09K 2200/0247C09K 2200/0625
53
PatentIndex Score
9
Cited by
31
References
36
Claims

Abstract

A silicone composition comprising: (a) a first silane of the formula: ##STR1## wherein: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from hydrogen, halo, and organo radicals; and n is an integer having a value of from 1 to 4; (b) a second silane of the formula: ##STR2## wherein: R 11 and R 16 are non-polymerizable groups and are independently selected from halo and organo radicals; R 12 , R 13 , R 14 , and R 15 are independently selected from hydrogen, halo, and organo radicals; and n is an integer having a value of from 1 to 4; and (c) a polysiloxane having at least two functional groups per molecule with which said first and second silanes are cappingly reactive; wherein: (1) the first and second silanes together are provided in sufficient quantity relative to the polysiloxane to react with substantially all of the cappingly reactive functional groups of the polysiloxane; and (2) the first silane constitutes from about 50% to about 98% by weight of the total weight of the first and second silanes.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A silicone composition, comprising: (a) a first silane of the formula: ##STR22## wherein: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10  are independently selected from hydrogen, halo, and organo radicals; and   n is an integer having a value of from 1 to 4;   (b) a second silane of the formula: ##STR23## wherein: R 11  and R 16  are non-polymerizable groups and are independently selected from halo and organo radicals;   R 12 , R 13 , R 14 , and R 15  are independently selected from hydrogen, halo, and organo radicals; and   n is an integer having a value of from 1 to 4; and   (c) a polysiloxane having at least two functional groups per molecule with which said first and second silanes are cappingly and non-hydrolyzingly reactive; wherein: (1) the first and second silanes together are provided in sufficient quantity relative to said polysilxane to non-hydrolyzingly react with substantially all of the cappingly reactive functional groups of the polysiloxane, and (2) the first silane constitutes from about 50% to about 98% by weight of the total weight of the first and second silanes.     
     
     
       2. A composition according to claim 1, wherein the first silane constitutes from about 70% to about 90% by weight of the total weight of the first and second silanes. 
     
     
       3. A composition according to claim 1, wherein the first and second silanes together are provided in sufficient quantity relative to the polysiloxane to react essentially completely with the cappingly reactive functional groups of the polysiloxane. 
     
     
       4. A composition according to claim 1, wherein R 11  and R 16  are independently selected from hydrocarbyl, fluorocarbyl, and fluorohydrocarbyl. 
     
     
       5. A composition according to claim 1, wherein R 11  and R 16  are independently selected from organo groups containing from 1 to 8 carbon atoms. 
     
     
       6. A composition according to claim 1, wherein R 11  and R 16  are independently selected from C 1  -C 8  alkyl. 
     
     
       7. A composition according to claim 1, wherein the second silane contains at least two acetoxy functional groups. 
     
     
       8. A composition according to claim 1, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , and R 10  are independently selected from hydrogen and C 1  -C 8  alkyl. 
     
     
       9. A composition according to claim 1, wherein R 6  and R 7  are independently selected from hydrogen, phenyl, and C 1  -C 8  alkyl. 
     
     
       10. A composition according to claim 1, wherein R 1 , R 2 , R 9 , and R 10  are hydrogen; R 4  and R 5  are each methyl; R 6  and R 7  are independently selected from hydrogen, methyl, and phenyl; and R 3  and R 8  are independently selected from hydrogen and methyl. 
     
     
       11. A composition according to claim 1, wherein R 11  and R 16  are independently selected from C 1  -C 8  alkyl and phenyl. 
     
     
       12. A composition according to claim 1, wherein R 14  and R 15  are independently selected from the group consisting of hydrogen, C 1  -C 8  alkyl, and phenyl. 
     
     
       13. A composition according to claim 1, wherein R 11  and R 16  are each methyl. 
     
     
       14. A composition according to claim 1, wherein n for each of said first and second silanes is 1. 
     
     
       15. A composition according to claim 1, additionally comprising (d) a third silane of the formula: ##STR24## wherein: R 4 , R 5 , R 6 , and R 7  and n have the same meanings as in the first silane formula;   one of the G and X groups is ##STR25## wherein: R 1 , R 2 , and R 3  have the same means as in the first silane formula, and the other of the G and X groups is R 11  having the same means as in the second silane formula.   
     
     
       16. A composition according to claim 1, wherein said polysiloxane functional groups comprise silicon-bonded functional groups including labile hydrogen constituents. 
     
     
       17. A composition according to claim 1, wherein said polysiloxane functional groups comprise functionality selected from the group consisting of: --OH;   --N(R') 2 , wherein each of the R' substituents is independently selected form hydrogen and organo groups, with the proviso that at least one R' substituent is hydrogen;   --SH;   --SO 3  H; and ##STR26## wherein each of the R" and R"'substituents is independently selected from hydrogen and organo groups:   with the proviso that said silicone functionality is ##STR27## only when the first and second silanes are present with residual acrylic acid groups deriving from the synthesis of at least one of the first and second silanes.   
     
     
       18. A composition according to claim 1, wherein said polysiloxane having at least two functional groups per molecule with which said first and second silanes are cappingly and non-hydrolyzingly reactive, comprises a linear polydiorganosiloxane. 
     
     
       19. A composition according to claim 1, wherein said polysiloxane functional groups comprise a terminal reactive functional group. 
     
     
       20. A composition according to claim 1, wherein said polysiloxane comprises a linear silicone with hydroxy functional groups at its termini. 
     
     
       21. A composition according to claim 20, wherein said linear silicone has a weight average molecular weight of from about 700 to about 300,000. 
     
     
       22. A composition according to claim 1, wherein the second silane comprises acetoxymethyldimethylacetoxysilane. 
     
     
       23. A composition according to claim 1, wherein said first silane has the formula: ##STR28## wherein R 17  and R 18  are independently selected from H and methyl. 
     
     
       24. A composition according to claim 1, wherein the equivalents ratio of acryloxy functionality of said first silane to polysiloxane functional groups non-hydrolyzingly reactive with said first silane is less than 1.0. 
     
     
       25. A photocured silicone material produced by curing a composition according to claim 1, under conditions curingly effective therefor. 
     
     
       26. A silicone composition, comprising: a polysiloxane having at least two acryloxy-reactive functional sites per molecule; and   a composition comprising capping species non-hydrolyzingly reactive with said functional sites of said polysiloxane, including acryloxy functionality and non-polymerizable functionality, which when non-hydrolyzingly reacted with said polysiloxane functional sites are cappingly effective therefor to provide acryloxy functionality and non-polymerizable functionality on said polysiloxane, such that the acryloxy functionality on the capped polysiloxane functionalizes from about 50% to about 98% of the reactive functional sites on the polysiloxane, and the non-polymerizable functionality functionalizes the remaining reactive functional sites on the polysiloxane.   
     
     
       27. A composition according to claim 26, wherein the capping composition comprises a silane compound having acryloxy and non-polymerizable functionality in the same molecule. 
     
     
       28. A photocurable polysiloxane composition, comprising the non-hydrolysis reaction product of the composition of claim 26. 
     
     
       29. A photocured silicone material produced by curing the composition of claim 28, under conditions curingly effective therefor. 
     
     
       30. A method of capping a silicone having active hydrogen-containing functionality with (i) acrylic functionality to render the silicone photocurable in character, and with (ii) non-reactive functionality, comprising non-hydrolyzingly reacting the active hydrogen-containing functionality of said silicone with: (A) a silyl diacrylate compound of the formula: ##STR29## wherein: R 1  R 2 , R 3 , R 4 , R 5  R 6 , R 7 , R 8  and R 10  are independently selected from hydrogen, halo, and organo radicals; and   n is an integer having a value of from 1 to 4; and   (B) a silane compound of the formula: ##STR30## wherein: R 11  and R 16  are non-polymerizable groups and are independently selected from halo and organo radicals; and   R 12 , R 13 , R 14 , are independently selected from hydrogen, halo, and organo radicals,   to yield a capped silicone having from about 50% to about 98% of the active hydrogen-containing functionality of the silicone capped with acryloxy functionality deriving from said silyl diacrylate compound, and the remainder of the active hydrogen-containing functionality of the silicone capped with capping moieties derived from said silane compound.   
     
     
       31. A method according to claim 30, wherein said silicone cappable functionality comprises a functionality selected form the group consisting of: --OH;   --N(R') 2 , wherein each of the R' substituents is independently selected from hydrogen and organo groups, with the proviso that at least one R' substituent is hydrogen;   --SH; and   --SO 3  H.   
     
     
       32. A method according to claim 30, wherein said silane diacrylate has the formula: ##STR31## wherein R 17  and R 18  are independently selected form H and methyl. 
     
     
       33. A method according to claim 30, further comprising forming a silicone composition which is photocurable to a gel, comprising mixing the capped silicone with a photoinitiator. 
     
     
       34. A method according to claim 33, wherein the photoinitiator is selected from the group consisting of benzophenone, benzoin, acetophenone, benzil, and substituted forms thereof, and mixtures thereof. 
     
     
       35. A method according to claim 33, further comprising exposing said photocurable silicone gel composition to radiation curingly effective therefor, to yield a photocured silicone composition. 
     
     
       36. A method according to claim 35, wherein said radiation comprises ultraviolet radiation.

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